Viability of a covalent chiral auxiliary method to induce asymmetric induction in solid-state photoreactions explored

Arunkumar Natarajan, Joel T. Mague, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The effectiveness of covalent chiral auxiliaries in inducing stereoselectivity during the Yang type II photocyclization reaction was examined using the benzonorbornene phenyl ketone (2) and α-adamantylacetophenone (7) systems. The outstanding ability of covalent chiral auxiliaries in generating high asymmetric induction in the photoproducts has been established in 7 of the 10 investigated examples. Three examples in which molecules crystallize with equal amounts of conformational isomers in the asymmetric unit, despite the covalently linked chiral auxiliary, highlight the limits of the use of the covalent chiral auxiliary approach for asymmetric induction in the solid state.

Original languageEnglish
Pages (from-to)2348-2355
Number of pages8
JournalCrystal Growth and Design
Volume5
Issue number6
DOIs
StatePublished - Nov 1 2005

Fingerprint

Stereoselectivity
Ketones
viability
Isomers
induction
solid state
Molecules
ketones
isomers
molecules

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

Viability of a covalent chiral auxiliary method to induce asymmetric induction in solid-state photoreactions explored. / Natarajan, Arunkumar; Mague, Joel T.; Ramamurthy, Vaidhyanathan.

In: Crystal Growth and Design, Vol. 5, No. 6, 01.11.2005, p. 2348-2355.

Research output: Contribution to journalArticle

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